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Tuesday was my last day as CEO of CircleUp (twitter.com/ryan_caldbeck)
405 points by rmason on Oct 15, 2020 | hide | past | favorite | 148 comments

Here's the blog post that goes along with that tweet stream:


Holy cow that feedback. It’s both great and awful at the same time. Great in that it was written as objectively as possible and concrete. Awful as in it was too long and he clearly put too much time in to it relative to how much the other guy valued him. I think the real purpose was to process his feelings and list out all the wrongs - I just think he should’ve separated them. Spend hours processing, spend no more than 15 min giving this jack off feedback.

Also hindsight is 20/20 but if you work with an asshole it’s not your responsibility to shield him. Escalate to the other board members and have them deal with him. He clearly values their respect so one of them (or better all of them) needed to sit him down for a talk.

Sounds like a case of "rich kid playing VC" syndrome, or something like that, because it's hard to see any competence in making money there (except maybe by inheritance or extreme hubris/sucking up)

> but if you work with an asshole it’s not your responsibility to shield him.


Let them hang themselves

Adding the google cache. Looks like the medium is down.


Simultaneously, we were forced to deal with a board member who was beyond counterproductive. After we bought him out fully in 2019, I sent this feedback email detailing the ways in which he had disrupted our board and company.

The former CEO should take down the feedback email, as he is exposing himself and others to legal liability.

He is not the only one who has had to deal with toxic investors who sit on startup boards. It's driven many good people away from companies they've founded. Sometimes the toxic board members are not newbies, either - they're supposed pros. Not sure what sort of due diligence can sniff these jerks out before they join the board, and maybe it's not even possible to turn them away if it's a condition of getting investment.

I think it is of great public service that the email is out in public domain. It warns many first time CEO's of the dark side of raising money from naive VC's who never ran a company before becoming VC.

The email also adds context to Vinod Kosla's famous message: https://techcrunch.com/2013/09/11/vinod-khosla/

Seems like many of the other VCs were pretty decent though. Eg encouraging the author to take time off etc. That's definitely adding positive value in my book.

This is one of the most honest and cathartic emails I've read. I genuinely think he should keep it up.

Some people naively view investment as "just money". This is an honest warning showing the real consequences of that incorrect view.

What legal liability? A lot of people especially here in the US are always invoking liability. What series of legal events do you imagine being initiated by the posting of this email?

Serious ? No more or less than giving a dentist a bad review, impacting their income and reputation. They will say I am not a bad person to work with and this inaccurate statements have affected my reputation.

A dentist can only sue you for a bad review if the statements are untrue, and harm his reputation. The email doesn't include the name of the bad guy, and even if it did, if the statements are true, then there is no lawsuit to be had. Sure, you could be sued by someone claiming that they're false, but under Anti-SLAPP laws if you prove that it's frivolous you can yourself be awarded $25,000.

Overall it's just very hard in the US to sue someone for telling the truth about how awful you are.

I’ve fought off a frivolous defamation lawsuit against me so I couldn’t disagree more with

“A dentist can only sue you for a bad review if the statements are untrue” and

“Overall it's just very hard in the US to sue someone for telling the truth about how awful you are.”

Huh. I stand corrected. Was your lawsuit about a bad review?

I've read through the transcript of a court case in Australia where the defendant lost 50k for some really borderline comments. Specifically, a vet was "grumpy", and charged 3x markup for some medication, which apparently was true but hand waved away in the hearing with the excuse around delivery and overheads.


That’s messed up. IANAL but don’t think that the outcome in the US would have been the same.

The feedback is simply not attributable for outsiders. I don't think there is a legal argument here. And even if the VC was identified, if the writer didn't invent any of those stories (you wanted inaccuracy, right?), there is nothing he is liable for...

Or am I mistaken about US law? I think it is even worse over there, you can basically write what you want, as long as nobody can prove it outright wrong. Just imagine all the New York Post articles somebody would be sued for.

Most outright defamatory articles just end in a "Welp, sorry?"-situation and nothing ever happens, because "It could have been true, right?"

The VC isn't going to sue the author of an email that didn't name them that called out their bad behavior. That would be news and link them to it. Most VCs at that company would think it wasnt about them because they aren't so badly behaved.

I'm thankful for that "feedback email", whoever that guy was, he either has a serious case of the Dunning–Kruger effect going on or he deliberately behaved that way to extract money out of a startup by being a total resource vampire for the group; like it was a strategy. Maybe that's how a certain number of VCs actually operate? They're just grifters all the way down.

Reading this is like reading about my own experience. I went through a similar period several years ago as an executive. I was leading engineering for three separate products and dealing with some very difficult stakeholders. I was also in a new relationship that I was trying very hard to maintain. The stress of all these things happening to me at once was colossal. I experienced a constellation of bad health symptoms. What I can't believe, in hindsight, was when I asked my doctor if this could be stress related. He asked, "do you feel stressed?" I thought for a second and said, "no."

I've never written anything about that time, despite wanting to, but this is the thread I wish I could write. Details aside the emotions are all the same. It felt cathartic to read this.

I had a business fail, an 8 year relationship break down (got cheated on) and in the middle of all of that they found a syrinx in my spine and a few months later I got diagnosed with Chrohns.

On my desk is a rock, just a hand sized piece of chalk off the foreshore near me but it has special meaning, I picked it up at 2am on the night I decided I wasn’t going to kill myself after flipping it from hand to hand for several hours while sat watching the moon on the water.

Now it sits under one of my monitors and when work starts to stress me out or life generally I pick it up and think back to 6 years ago.

These days my health is under control, the chrohns is stable, the medication works for quality of life, I have a good well paid job and I met the love of my life so between now and that beach is 6 years and a universe apart but man, you don’t see the signs until afterwards eh.

No one knows what the rock means to me, to everyone else it’s just a paperweight.

Thanks (to both you and the parent poster) for sharing your experiences. I know exactly how helpful seeing this kind of post can be for people who are struggling.

Agreed! As someone who is in a tough spot right now, this post really hit home.

Thank you for sharing this. I admire your strength.

What symptoms, out of interest?

Various digestion issues and stomach pain. I'd find myself getting dizzy and lightheaded out of the blue while doing nothing more than sitting. I'd have trouble concentrating when talking to someone and have trouble remembering what I was talking about. I'd wake up in the middle of the night nauseated. I'd have episodes where I felt like I had to focus on my breathing or my body would forget to breathe.

None of these persisted. They'd all come and go. When I went to the doctor, all tests showed I was fine, which stressed me out more.

I have persistent anxiety and every few months my body will either revert to one of the symptoms you described there or invent something entirely new and fun for me out of the blue. It took a while for me to realise what was happening and actually start taking care of myself - it's criminally easy to get stressed behind your own back. You don't realise you're in the thick of it until it's too late.

The 6-page e-mail sent to the difficult former board member is interesting: https://docs.google.com/document/d/17tEc9ETL4tjfTmNbpwJJ5OSx...

Given that he posted the e-mail contents online and wrote it in a way to narrate the board member's own bad actions, I'm assuming the real intent to was to warn others against working with this person. He stops short of naming the difficult board member, but it wouldn't exactly be difficult to figure out who it was from all the clues.

Some people are agreeing with you, but I actually don't agree. I looked into this and it's actually quite difficult to definitively identify who is being referenced. There are a few seemingly conflicting bits of info in the letter, like the person is a novice VC investor ("I recognize ---- is your first experience in venture, or as a professional investor") with the fact that they are also the lead investor in one of their rounds ("I still can't believe that is true for the lead of our Series ---"). As far as I can tell, these seem to be mutually exclusive: the leads of all the rounds seem to be veteran (or at the least very seasoned)VC investors.

Theoretically this would be easy to figure out if you had a yearly listing of board members which I imagine should be public, but that doesn't appear available publicly. The only listing of the board I can find is this news article [0] from 2015, but again, none of the people listed there can be definitively identified as the one being referenced.

As further evidence of how murky this is, several people in the comments below have named different people as the person being referenced. One commenter has edited their comment to change the person being accused.

If the author of this email wanted to point a finger at a specific person, they did a bad job.


Hopefully this reply doesn't get me in trouble on HN...

But I strongly disagree with you.

Collaborative Fund led the Series C round. Jay Kim was a fairly fresh venture investor at the time; the model and operation of NXC/Nexon's investment arm was quite different to the traditional VC. Based off the timings, it's highly likely this is the VC who the e-mail refers to.


sounds like Craig Shapiro is the likely culprit here

Very doubtful. I think you misunderstood the tweet; the person who posted that tweet is asking the founder and leader of Collaborative Fund to be responsible for the actions of his partners. Craig isn't the one who was sitting on the board.

nope. He confirmed its him but denies the accusations https://twitter.com/cshapiro/status/1317212694529802242?s=20.

I agree. I also tried to figure this out and couldn't narrow it down to a single person.

However, while the lead investor companies are established, the "partners" of the lead investors listed on crunchbase do seem to fit the fresh investor note. Especially since Series B and C were 5-6 years ago.

Mmm, yeah. I wasn't considering the series C because the timelines didn't really add up, but I took a second look and it actually fits the points in the letter.

An extra bit of complication seems to be that CircleUp itself seems to be some sort of VC-like operation, so at times I wasn't quite sure if some of the funds they were raising were for CircleUp or their clients.

Time to rewatch Inception.

Three names have been named. Two of the names are from the same throwaway account (unless something was changed with edits).

Let’s not do that. I’m incredibly appreciative of OPs transparency here. As a person who is susceptible to the same degree of stress and mental health toil, let’s not make the story about the investor but rather around the stresses of being a CEO.

You can't control what people are interested in, what they want to know more about.

I bet Facebook executives beg to differ

Sure you can, to a degree substantial enough to afford the entire advertising industry.

I agree that the problematic investor shouldn't be outed here. The investor isn't here to defend himself, and outing him will cause him irreparable (and perhaps undue) reputational damage.

[edit] Is giving the accused a platform to defend himself that unpopular of an opinion? Online shaming often gets out of hand and goes too far. I recommend this TED talk: https://www.ted.com/talks/jon_ronson_when_online_shaming_goe...

What forum should he be outed in exactly?

There are a couple options that come to mind:

1) Contact the accused party and ask him for a written response. By giving him the opportunity to defend himself, you get a more balanced view and decrease the likelihood of cruel & unusual punishment.

2) Out the investor in private forums where data/information that arises after the publication of this article can be fully considered. YC and many other founder networks have investor databases for this purpose.

1 isn't a terrible idea in most circumstances but with investors you're more likely to get a C&D than a fair response given the line of work and the importance of reputation to the process.

2 - no, I disagree strongly for two reasons:

Keeping information in a quiet private forum makes it inaccessible to people at large. This means the next CEO who runs up against this investor is mostly completely unaware of their past actions.

And, honestly, hackernews is probably the single most relevant forum you could find to discuss this on - it has a general lean toward tech but it is run by ycombinator which is specifically interested in all things investment.

> Keeping information in a quiet private forum makes it inaccessible to people at large. This means the next CEO who runs up against this investor is mostly completely unaware of their past actions.

I agree this is the downside of my proposed approach. But, the alternative is a world where someone's reputation can be irreparably damaged by unsubstantiated claims made by one person.

Do you want to live in a world where someone's reputation and livelihood can be destroyed by unsubstantiated claims? You may think I'm overstating the potential damage, but I think people generally underestimate the damage the internet mob can inflict on a person.

There are some societal tools that exist to fight against baseless slander in a public forum but, tbh, the US has resisted adopting those.

I would rather live in a world where the powerful can be baselessly attacked compared to a world where the weak are unable to fairly attack them - if we need to err on one side or the other I prefer to put up with trolls and scammers.

Except the powerful will simply use those tools to baselessly attack the weak especially those that pose problems to them. They, after all, have the money and influence to pay for much more professional attacks than the weak can scrounge together.

I don't see this as a case where a weak party is unable to fairly attack the powerful.

Even without outing the investors, many founders are currently doing the necessary research to identify the investor and will blacklist him.

I think we should keep in mind that:

1) The accusations are currently unsubstantiated

2) The reputational damage to the investor is already significant and largely irreversable

3) Outing the investor here will significantly increase the reputational damage to the investor

Given the above, I really don't see how it's fair to out the investor before substantiating the accusations or giving the investor time to respond.

This is similar to how priests were quietly shuffled around parishes. Yes, the priest's activity were criminal so it's NOT 1:1 of a comparison. However, keeping shitty people protected by keeping the info private does nobody any good

EDIT: left out the keyword NOT in the 1:1 comparison

> Keeping the info private does nobody any good.

I'm saying that we should keep the identifying info private until the accusations are substantiated.

The internet mob is merciless, and will very likely ruin this guy's reputation once he's outed.

By outing the guy, you are presuming him guilty and inflicting steep punishment when he could be innocent.

> I'm saying that we should keep the identifying info private until the accusations are substantiated.

How do you substantiate an accusation like "you insisted on talking to me at 3AM local time after I just stepped off a plane after a 18 hour flight" (or whatever the deets are)?

> By outing the guy, you are presuming him guilty and inflicting steep punishment when he could be innocent.

In general, yes, but in this case the most convincing candidate is a billionaire. He'll be fine.

The author didn't out them, and they were the people that feel wronged by them. Why do you feel the need to do what the author chose specifically not to?

Why not both?

Well. It seems like you can't narrate the latter without the former. What would you propose?

It's clear that people in the industry will be able to figure out who the letter is addressed to - and I would be surprised if the CircleUp CEO didn't realise this. So the censorship is mostly for show.

The fact that the VC isn't named, makes it difficult for them to reply in a public way and respond to some of those points.

It seems like if many people don’t know, then it actually makes a difference that they don’t know. I don’t know the details but it seems possibly important, not just for show?

See: https://en.m.wikipedia.org/wiki/Missing_stair

> and I would be surprised if the CircleUp CEO didn't realise this.

That was the point I was trying to make:

The CEO went out of his way to make the board member as easy to identify as he could, short of spelling his name out.

I'm not suggesting that people try to reverse engineer it, but clearly the open letter was meant to be partially retaliatory and partially a warning to others in this space.

Given the timeline, that he was lead investor, the name length, the experience of the VC, the current and past board members, it’s easy to figure out the missing name. https://en.m.wikipedia.org/wiki/CircleUp Confirms the name which would also fit in the redacted parts of the email.

If you highlight the name, the highlighted text is {{14}}. I don't think the lead investor's name is necessarily 6 characters. FWIW, I was deeply curious about who the investor was and spent some time investigating who lead the fundraising rounds on Crunchbase, but I couldn't narrow it down sufficiently.

I got curious as well.

One of the funds mentioned in the wikipedia article and that also matches the description from the email removed CircleUp from their portfolio website in 2019. You can look it up on the Internet Archive.

thanks, I was able to figure it out.

Where are you seeing the current and past board members? That’s what I’m trying to diff against but I can’t find good sources.

Not just for show; doing it this way likely spares that person's SEO.

Aren’t Google Docs unindexed unless published to the web not shared as viewable links?

I suppose so. I was thinking more along the lines of his name not appearing in this discussion's title means people searching his name might not find this discussion.

I think just publishing the event without posting the email leaves enough of a trail for another CEO to reach out and ask "Hey, we're going to work with XYZ and know he used to be on your board. Any advice for us?"

Nobody likes to date people who are always trashing their exes. Board members end up choosing the CEO, do they not? There are degrees of dirty laundry airing that could end up burning bridges with people you've never even met before.

Meanwhile the next CEO knows there's a rat, and can work out for themselves who that might be before their first 100 days are up, by which point most managers have been typecast. After that it's very hard to fully take advantage of major new insights you've had. It's an uphill battle to make major changes to your style of management.

Nobody likes to date people who are trashing all their exes but one is fine.

Fair enough. But you also are careful when they trashed their last ex.

Name the board member. The former CEO can be dignified by keeping his name confidential , but this is a founder and entrepreneur discussion forum and this deserves discussion about this individual. It is also relevant to the story.

There is absolutely nothing wrong with knowing about, and discussing who it is and possibly who else has had the same experiences - as long as it isn’t mudslinging but a professional discussion. Similar to the letter.

>> There is absolutely nothing wrong with knowing about, and discussing who it is

You should keep in mind that the investor may actually be innocent here. Imagine if the CEO was a sociopath who is both adept at manipulating public opinion and out to destroy the investor's reputation.

I'm not saying this is fact. I'm saying it's possible.

Outing the investor here will cause significant, irreparable reputational damage to the investor.

Given that the accusations are based on unsubstantiated claims, outing the investor is wrong.

Please don't underestimate the consequences of your actions. You may see it as just 'discussing some random topic on a forum'. But, doing so could be ruining an innocent person's life.

Naming the investor is counterproductive.

Bad investors, bad board members, and even bad incubators are a dime a dozen.

Naming this 1 investor focuses the discussion on that single investor, rather than bringing awareness to the situation itself, and how commonly these things happen (yet how rarely anyone talks about it).

Indeed. It didn't take me long to figure out who the seeming douche bag of an ex-board member is, despite being half a world away from the US and Valley intrigue. Yet, if Ryan Caldbeck chose not to name and shame, it is not my business to out someone.

I liked someone's comment about preferring to let the focus be on Ryan's journey, and I suppose that many others here must be feeling a sense of kinship with a fellow entrepreneur as he described candidly and courageously his version of "The Struggle."

Sure, so that the lesson isn't lost, though, we may want to learn from Ryan's sobering experience and think harder about this too: Which investors we choose to collaborate with, come due-diligence time.

That's a very good letter. Very revealing at the board level. It's amazing how childish and unprofessional the board member had behaved.

Meh. I read this as a bunch of whining that reflects poorly on the CEO. He even admits to taking this investment and giving up a board seat without ever meeting in person. Embarrassing frankly.

Yeah, totally right! All those personal and health issues... How dare he whine about it now. Like as if he is some sort of... oh i don’t know... a human being with emotions and feeling. Gods this is CEOs have become now.

EDIT: #sarcasm if it wasn’t obvious.

I’m referring to the letter to the board member itself, which apparently wasn’t #obvious to readers on HN.

I'm not a CEO, nor do the livelihoods of people depend on me.

But I feel the pain everyday of having to answer to my managers who are constantly asking for status on my projects. I care about my managers but I don't care about the projects. I hate my work.

There are so many things in life that I am curious about like singing, drawing, gardening, bird watching, etc. I'm not good at any of them (nor do I wish to be) so they won't bring me any income. Every day I put my curiousness aside to code some stuff to make my managers look good.

I can't quit my job to take a break because my wife and kids depend on my salary for money. My neighbors are suffering more because they are not in tech. They are trying so hard to have my life and I try my best to help them get into an industry I don't even like.

Money brings so much suffering and our entire society is built on it. Society is greedy and wants to expand infinitely too! Everything in nature must eventually be owned my someone.

It seems like the only way to escape is to become a CEO, make millions, and buy a bubble of eternal happiness as Ryan has done.

I hope I don't end up behaving like his former board member.

Why not just downgrade your lifestyle to be in a cheaper situation? Easier said than done obviously, as that initial downgrade feels like a big hit. And ofc you might have extenuating circumstances that prevent it. But otherwise, I've found that you simply acclimate over time. Then you can give yourself breathing room to take time between jobs, or perhaps move to a lower-paying job you actually enjoy.

For context I am a developer in the Silicon Valley. The more I see around me and our nation at large, the more I am forming the opinion that greed is THE defining attribute of our time. The way the economy and society is structured, there is absolutely no breathing room left for anyone to perform any activity except to exist in the service of a paycheck. Why? because of greed. Because of greed and the blindness it brings with it, any attempts to build even a slightly more benign economic arrangement gets immediately labeled as "socialist" or some such. Not to mention the absolute beating our natural environment and habitat is taking in the process of servicing this greed to accumulate as much as you possibly can.

I am also a developer in the Silicon Valley and I agree with everything you said 100%. It is a lonely place to be if you are not greedy.

It is a transient response I feel to the money printing since, well, technically 2001.

Why now? Greed has been prevalent throughout history.

Thanks for your input. I've never really thought programming was much of a rewarding career for those capable yet wholly nonplussed. I hope, predicated on the notion that this isn't for you, you don't give up on developing another career path

You only have one life to live. You don't have to spend it in slavery to possessions.

Interesting read, but one thing that always strikes me reading this kind of story is how invested founders are in things that -- I'm sorry to say -- are not exactly earth shattering. I'd never heard of CircleUp before this, and their slogan "Creating a transparent and efficient market to drive innovation for consumer brands" still doesn't tell me what exactly it is that they do. Obviously they have investors and customers who found it worthwhile, but is it really worth sacrificing your health & family on this altar?

That said, I do wonder how Elon Musk, who's simultaneously trying to send humanity to Mars, convert the world to electric cars and solar panels, and create direct neural uplinks doesn't crack from the pressure though.

> That said, I do wonder how Elon Musk, who's simultaneously trying to send humanity to Mars, convert the world to electric cars and solar panels, and create direct neural uplinks doesn't crack from the pressure though.

Not to mention what I would consider the most important commitment for any parent: how does he find enough time to be a good father to his 6 kids?

Easy answer: he’s not a good father. It’s his choice. I don’t think there’s anything particularly wrong about it, but it’s sad for his kids. Steve Jobs was a shitty parent as well. You can’t have a balanced life if you want to be extraordinary. It’s literally impossible.

> I don’t think there’s anything particularly wrong about it

I'd say that not being a good father by choice rather than necessity could be considered pretty wrong.

As a father of three, I often feel I don't have enough time to be a good parent to that many. How does anyone have enough time to be a good parent to 6 children while also working? (That is, assuming "good" means more than "pays the bills and isn't a complete douchebag").

I’d say Elon Musk has been acting more and more erratically as time has gone on. Just this week he changed the price of the Model S to a meme, $69,420. Seriously.

seriously good marketing, actually.

Here we are deep into a comment thread about a completely different company and you are spreading elon's message about the price chance of his product for free.

thats a genius move by musk.

Yes for all the people who didn't know about Tesla or Elon Musk. Now they know, and maybe they'll buy a Model S.

There's more to it than you're giving him credit for.

You call it erratic. Others see it as eccentric. And, that draws eyeballs.

There's more to life than trying to improve the human condition. People value different things, and it's very possible he will proudly look back on his time spent on CircleUp.

Put another way, not everyone wants to do the same things you do.

The world of silicon valley-style startups and tech entrepreneurship is so full of drama and intrigue. The entrepreneurship ecosystem is full of narcissists, blowhards, and self-important people who believe that since they are managing other people's money they therefore have more wisdom and insight than anyone else. Board members who feel that their role as board member grants them instant authority and credibility on all topics. CEOs who believe that their title means they deserve respect. And a range of hangers-on and wantrepreneurs who want to be part of the scene but have no real idea or knowledge on how to build a business.

Some startups are built to grow. Some are built to flip. Some will never go anywhere but fill people's pockets and egos. But many many more just fail.

There is little relationship between the alternate reality that is the startup world and the more mundane, sedate, and less interesting traditional business world.

Tweet storms and email chains like these read like the startup version of Jersey Shore or Housewives of OC.

(replying to myself here)

When will people understand that the VC industry is a form of money management? It's an investment vehicle focused on generating a particular kind of return by investing in a particular kind of company.

VCs don't invest in businesses as much as they invest in return-generating vehicles. If you can find a way to turn a grilled cheese business into a billion-dollar return-generating vehicle, then the VC will invest in it. It doesn't matter if it's an actually sustainable business or even really a business at all. Heck, you could be giving away grilled cheese and putting advertisements on the bread and if it fits the VC model then VCs will invest in it[1].

This is why "businesses" like WeWork are so divorced from business reality. Because they don't need to follow the typical path of traditional businesses, which are dependent on cash flow and customers and mostly industry or region-specific competition. Banks can loan to traditional businesses they understand. VCs invest in the businesses that don't fit those molds. This is why venture investing exists - to chase those non-traditional businesses that have the promise / potential to generate huge returns. The specifics of the business really don't matter.

It follows then that if you're building a VC investment-return generating vehicle then what you're doing is not the same as building a "normal" business. You're in an ecosystem dominated by the needs for big returns. Board members don't know about or care about traditional business needs. They only care about the dynamics of investment return vehicles. This reality is not the same as the traditional business reality.

[1] https://www.crunchbase.com/organization/melt-shop

While I feel for the guy's struggle with cancer and the fertility issues he and his wife went through, I'm seeing the same tone in some of his other tweet threads (and threads from other people) and it's starting to feel like an intentional pattern done for audience building.

Which, I don't doubt he went through all this, but just can't help the bad taste in my mouth given the "I'm just selflessly saying things to help others" tone.

But hey, maybe I've just grown to be overly cynical after spending too much time around growth marketers.

I'm equally cynical. But is it a chicken / egg question? Does attempting to be genuine, vulnerable and reflective lead to a bigger audience, or does seeing that the audience gets bigger as a result lead a person to be more genuine, vulnerable and reflective - to a point of artificial oversharing?

I guess the other question is... if there is good to be done, and being this kind of person causes a certain amount of help to hurting communities, does this form of vulnerability capitalism have a downside? (assuming its done with respect to the person's family and friends, who never asked to be thrust in this weird limelight)

And a question I often have to ask myself, what if it is nothing but genuine? How does one call out BS without trampling on the spirit of the genuinely hurting?

"Vulnerability porn" is an intensely annoying trend among Twitter tech personalities.

Eyeopening. When "follow your Dreams" leads to this....well did you really dreamed about it that way? Where is the fun? Looks like one becomes a "business" brainwashed robot spending way to much lifetime at doing ???????? just playing 'respect' to ego psychos for an in fact empty basket filled with $$$ paper.

Listen to signals your body sends, if there is no fun soon, it means STOP. Oh yeah you can watch datapoints, brainscans and talk to experts for years, but listen to what you feel is enough. It is hard to beat that "intelligence" sensor encorporated in the human shaped by thousends of years of evolution.

I wish this guy al the best, this maybe is the best thing he ever did.

I hope he can find back to a more satisfying life with lots of lifetime, enjoying doing fun things with his family!

No need to track down that destructive board member. He is sitting at work right in front of you on a basket with $$$, you listen to him as you think you need it for food and if you are priviledged for "dreams".. maybe just look in a mirror ?

Here here! Great lesson for all. Also, very damning to peak into the kitchen to see the sausage making. If starting a high growth company is this demanding and obnoxious, what’s the point? “Making an impact” is the best answer, but then it should be something more humane than financial.

Wow, this really struck home with me. I left a FAANG about a year ago to be employee #1 at a startup. 6 months ago, after some headaches and vision issues, I was diagnosed with a brain tumor. My work has been great through all this, but I can't imagine the additional stress of being a CEO whilst dealing with all that.

That’s terrible news and I’m very sorry for you. I hope your prognosis is excellent.

The more I work in this industry the more I resent upper management and boards. Not just the guy he's writing about, but even just venture and this guy himself. Is this guy really contributing so much to society that it's just he has enough money to "call in the best doctors in the country" while the workers are left with squat? It seems like the people who work the least reap all the benefits.. Maybe covid's just got me being cynical though. I hope his prognosis is good.

>It seems like the people who work the least reap all the benefits..

How exactly did the reading of this post make you conclude he did the least work?

You do not comprehend the concept of risk. As in, his life-continuum determined for him the affordance to seek the best treatment after compounding time in a direction you or I could never perceive. In fact, this is what makes entrepreneurialism so virtuous.

I am really starting to get agitated by this pettiness on HN. It didn’t used to exist in tech.

I was wondering where I knew that name from... there's a module about Ryan & CircleUp in the HBS Disruptive Innovation Course - https://online.hbs.edu/courses/disruptive-strategy/

It was one of the more interesting companies profiled and I found the module very cool. If you read this Ryan - thanks for being part of it, and all the best for the future.

What did you think of that class? I’m doing a Reforge program now and hungry to keep doing similar. The Innovation Course looks pretty awesome.

First thanks so much for writing this. The gilded world of unicorn CEOs seems all roses and wine from the Techcrunch armchair VC/outside world, so it was eye-opening to read an intimate account of the cold, brutal reality of being one.

That said, I have one question. What on earth was the co-founder doing? Isn't it the whole point of having co-founders so that you can share the trauma? Why did the CEO have to suffer through so much pain all alone?

From much experience with startups, founding and co-founding is a mental mind-f*ck at all times. Even founders of good companies are under constant stress to keep the thing proposed up. The stress and drama of running a company completely f's your world up long into "success"

Thread Reader really helps for this, given the length (and some weird issues at least for me with twitter web).


> When at a board meeting at USV you stopped the meeting and said “guys we just aren’t focused on the right issues, this company has less than 6 months left.” One of the other board members said “ What are you looking at?” (You later realized you weren’t doing the math correctly).

This would be an immediate red flag. How do you handle this type of issue?

I always wonder why people use Twitter for these braindumps? Do these threads just lend themselves well to starting and typing until it’s all off your chest?

I quite like it. It promotes a concise writing style which wouldn't be as acceptable if it were on a blog without character limits.

Whenever I write something like this I've found I end up constructing each tweet a bit like a lengthy bullet point. I cut everything unnecessary and try to make my point as clearly as possible in as few words & tweets as possible.

When I write a blog post I naturally end up optimising for writing quality, and what could have been 5 tweets ends up as 1,500 words.

The audience is on Twitter. More likely to get engagement from tweets than via a blog post; because it's off platform, most people won't click it. There's also virality on Twitter from sharing specific parts of a thread in the form of retweeting and liking.

I'm happy everything worked out for you Ryan. But I was left so queasy by this whole read.

This is presented as a victorious journey. By the end of it he's got his health back, his kids, an easy job, lots of money. The company's in good shape - everyone's a winner.

And you're telling readers - it's GRIT! I'm a super Gritter! I never give up!

Mate, you got so lucky, to be alive, to have kids.

Yet you lost years of your life, plus all your kids' early childhood fretting over terrible bosses. And by the end of it you're still wondering whether in future VCs will find you worthy of investment.

And in our day and age you're considered a winner!

You're the person YC points to and says - See him, you could be like him one day!

"Life, if you know how to use it, is long.

But one man is possessed by an avarice that is insatiable, another by a toilsome devotion to tasks that are useless;

one man is besotted with wine, another is paralyzed by sloth;

one man is exhausted by an ambition that always hangs upon the decision of others, another, driven on by the greed of the trader, is led over all lands and all seas by the hope of gain;

some are tormented by a passion for war and are always either bent upon inflicting danger upon others or concerned about their own;

some there are who are worn out by voluntary servitude in a thankless attendance upon the great;

many are kept busy either in the pursuit of other men's fortune or in complaining of their own;

many, following no fixed aim, shifting and inconstant and dissatisfied, are plunged by their fickleness into plans that are ever new...

Ask about the men whose names are known by heart, and you will see that these are the marks that distinguish them:

A cultivates B and B cultivates C; no one is his own master."

-Seneca, On the Shortness of Life

I don't want to digress too much here but I thought this was interesting:

> Believing that to attract a great CEO we would need more than two years of runway

What is involved in this process that takes 2 years?

It isn't that the process takes two years - I'm guessing they were talking more about being a good career move for a CEO candidate:

A great CEO has many options in front of them of what to do with their career. Asking them to take on a company that doesn't have much runway limits the time they have to get in, become the new leader, and mold the organization. Therefore, it is not likely to be their best option, which means the candidates who are interested are more likely to be not-so-great CEO candidates.

Got it, that makes a lot more sense.

The process of finding a 'good fit' CEO could very well take a very long time though. But your point is valid as well - nobody wants to jump onto a ship that's about to go down.

I think what he's saying is that no-one would be willing to take over as CEO unless they had two years of runway ahead of them.

In addition to the other answers, it sounds like they knew they needed more time to execute & validate the pivot.

Let the original founder/visionary execute the pivot and then hand off the reins, rather than pull someone new in and try to brain-dump how you want them to pull off the pivot that mostly exists in your head.

> What is involved in this process that takes 2 years?

He's not saying the process will take 2 years.

He's saying that no reasonable CEO will sign on to a company that is months away from going bankrupt. Two years of runway is long enough for a new CEO to find their feet, set direction, and work on profitability and/or fundraising.

If the CEO arrives with only a few months of runway, their first tasks will be to cut burn rate by laying off many of the employees. That doesn't create a good first impression.

Twitter is the worst for long form messaging.

This exact same comment is found in literally every one of these types of threads. And the answer is fairly obvious: audience, and forceful conciseness thanks to the platform constraints. I really wonder when this cycle of typical HN cliches will go away.

> audience, and forceful conciseness thanks to the platform constraints

It might be cliche because its a problem often seen repeated. This is how you get important messages not read or have them taken out of context, even by your intended audience. (we obviously disagree and both perspectives are opinion based)

Or maybe... get this... people have an opinion? Mind blowing right?

Sounds like confirmation of an opinion to me if it needs to be said a lot.

I didn't mean to offend. My point was that these cliche comments rarely (if ever) contribute anything to the actual topic being discussed.

I agree that the UI sucks but I like the constraints. It gives no room for filler text and every paragraph/tweet needs to have its own point.

Is it just me, or do people in the tech startup world know this personality type all too well?

I see them as slightly less crazy, but just as annoying as our dear president. Hopeless narcissists who read Ian Rand and The Prince in their teens, and think of themselves as Tony Stark when they're really just Russ Fucking Hanneman.

The VC firm in question is trivial to figure out. Just look for a firm that had a board seat that is no longer listed on the site and that does not list Circlecup on their site.

Yeah, well, fuck the whole thing.

So this guy fired a college buddy who chose to work for him instead of a better-paying job. "I believed in you". And the story just moves on, like it's a colour detail to the whole thing?

Does this person get a royal severance package? Does the struggling CEO help them land on their feet? That's the kind of stuff I want to know.

With those little details left out, it's just another powerful individual complaining about how hard it is to be powerful and wealthy.

I'm trying to think of ways to make this comment more even-keeled and less likely to be downvoted, but I honestly can't. This kind of stuff bothers me to my bones, and while I definitely support this guy being honest, so much, because I do care about mental health, I can't get past the "here's my hero story, forget about the consequences for the small guys" aspect of it.

It’s called leadership he created ex nihilo. Prey tell, sir, who have you ever led to be so prudential in your judgment?

I don't see how my accomplishments, or lack thereof, have any bearing on my moral beliefs and expressing them.

That said, I was in a bad mood, and in hindsight I shouldn't have judged based on so little information; I don't know what /actually/ happened. mea culpa.

Accomplishments provide empirical knowledge of one’s hypothetical and private judgements. How else can one know one’s wisdom if not through its demonstration?

> When at a board meeting at USV you stopped the meeting and said “guys we just aren’t focused on the right issues, this company has less than 6 months left.” One of the other board members said “ What are you looking at?” (You later realized you weren’t doing the math correctly).

This would be an immediate red flag in my book. How do you handle this type of issue?

A gem of a writeup by Ryan. I read through the whole thing, including the emails he shared. Some snippets below for folks who may not read the whole thing.

The people we let go had joined because they believed in our product and mission. They had done nothing wrong, yet suddenly there was no longer a place for them. I remember letting go of someone I had known since college. She turned to me and said, “I took this job over something that paid more, and now what should I do?” These agonising decisions kept me up at night for weeks, and I know it was much harder on those affected.

That group of professional challenges was more difficult than anything else I’ve faced in my career. At the time, I told a teammate that it felt like I was playing seven-dimensional chess because of the complexity of the negotiations combined with so many conflicting challenges at work.

I was also juggling personal challenges that were far more stressful than the hurdles at work. It started with absolutely brutal fertility issues that my wife and I went through, beginning in 2016. One of those tests revealed unexpected, terrifying information. I was diagnosed with cancer. I only remember a pair of words from the first conversation with my doctor: “two tumors”.

For the next several months, my emotions would sometimes pour out in a tidal wave of tears and yelling. Anger, frustration, fear, confusion — there were so many feelings to contend with.

I worried that the team would use my diagnosis as an excuse to throw in the towel, that my health would become a distraction, cause the company to fail and make things that much worse.

To this day, I cry every time I go to the cancer center at Stanford.

I hadn’t had a headache in 20-plus years and now I couldn’t go through a full day without experiencing crippling pain in my head.

By the end of 2017, I was completely worn out.

Persistence was my superpower. But now I’ve now come to understand that persistence is a double-edged sword, and my decision not to take a break, to not take more off my plate, hurt me, my family and the company. That was the biggest mistake of my career.

depression and burnout can make even small challenges feel like a big deal.

I had gotten to a place where I only focused on the losses and couldn’t accept positive things.

my daughter looked at me and said, “Daddy, you always look so sad”. She was five. It was the push I needed to change.

A successful and healthy transition requires one to live in the nothingness between the end of one period and the beginning of another.

FINALLY HIS FIRST EMAIL(feedback to the board member) IS AN EXCELLENT READ.

So many fine people on both sides of the Silicon Valley soap opera

> She turned to me and said, “I took this job over something that paid more, and now what should I do?”

What a shitty thing to say. I'm sure she was an adult when she joined, fully capable of making her own decisions and weighting up pros and cons.

If you read the email it states that the investor was a lead. Series A was led by USV and the email already ruled them out. This investor sold right during or after the series C. might be Brendan Dickinson from Canaan for the Series B.

Doxxing on HN feels like it should have an extremely good reason to do so, IMHO. Unless you are 100% sure you are correct, all speculation should be avoided since you could cause severe damage to others by misattribution.

From reading other posts by Ryan, he seems to be trying to talk about the general problems he faced that simply don’t get surfaced often (for example, due to the associated risks to your career.) He provides enough detail to help anyone likely to be in the know to identify the person.

There is a very difficult balance to make, and he has clearly been careful about judging that balance, and getting feedback from others on that balance.

Canaan still lists CircleUp as a portfolio company and the partner is Deepak Kamra. Curiously, a 2015 article lists the Canaan board memeber as Daniel Ciporin. Curious.

Ryan explicitly calls Dan Ciporin "a great board member" in his blog post.

The selected passage:

"A great board member, Dan, called me to say, “Ryan, I’ve never in my career seen a CEO as worn out as you. Please, you need to take a sabbatical — at least six weeks”. He, and other board members, tried so hard to do the right thing and convince me to take care of myself."

Further, on LinkedIn, Dan still lists himself as a current member of the Board of Directors. CircleUp is still listed as a current investment on Canaan's site.

I have not worked with Dan but I have worked with Canaan. They have always struck me as founder-friendly. Indeed, they have several notable repeat entrepreneur relationships. It seems unlikely they would tolerate the sort of behavior Ryan described.


Conversely, Collaborative Fund led the Series C in November 2015. Note that, in Ryan's letter, he cites board issues from 2016 to 2019. Further, Collaborative Fund no longer lists CircleUp anywhere on its site.

Per Crunchbase, Jungju (Jay) Kim was the board partner for Collaborative's Series C investment in CircleUp.

Note that, per his LinkedIn, Jay became a VC at Collaborative in 2014.

Plausible. The guy has a wikipedia page that was clearly written by a PR agency:


There's way too much detail and it's all incredibly flattering, stuff like:

He is known for strategic investments that aren’t limited to gaming companies, and he has acquired firms and invested in various fields. Being an avid Lego fan throughout his life, in 2013 he purchased Bricklink, the world’s largest online marketplace for Lego toys.

It sometimes surprises me that wikipedia can be gamed this easily.

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